Friday, April 30, 2010

The Bet - Chapter 22 (Saturday – week 3 Part 2 of 6)

The Bet
by Karen Singer

Chapter 22 (Saturday – week 3 Part 2 of 6)

Chad’s first stop of the morning was at the ATM machine at his bank to get more cash for his wallet. Getting his bank card out of his wallet was difficult, but when it came time to push the buttons on the machine, he decided to use the tips of his nails instead. It felt strange to push the buttons using only his nails, but surprisingly, it went very easy. So easy in fact, that he decided to remember that little trick.
Instead of stopping for breakfast, he decided to skip it completely. Eating or drinking anything would only make him need to pee sooner, or worse, mess himself. Keeping that to a minimum, especially in public would be a big help. From the bank, he drove to the drug store to get his diapers. Most of the things on his list he could have gotten at only one drug store, but he didn’t want to be seen buying diapers along with all the other feminine things he needed. Just going into the store dressed as he was would be bad enough. Besides, he would have enough trouble just carrying the two bags of diapers.
As he pulled into the parking lot, he distinctly remembered going into this store last week. What a nightmare. He had left his purse behind in the car and had so much trouble carrying the bags of diapers that he had dropped and broken his cell phone. No use leaving his purse behind today, he was wearing a damn dress. As he got out of his car, he prayed that people would see him as a woman and not as a man wearing a dress – even at first glance would be helpful.
He walked boldly into the store and headed directly to the adult diaper aisle that he knew so well. The store was a bit more crowed already than he would have liked. He shouldn’t have wasted so much time hanging everything back up in his closet. He could have been here earlier when there were less people around. A lesson learned, but it was too late now. Today, the aisle was well stocked with the diapers he needed. Why couldn’t it have been that way last week? He grabbed two packages, and holding one in each arm, headed to the checkout counter.
Again, he had to wait in line. Why couldn’t they have more than one register open in these stores? The woman in line in front of him turned around just to see who was behind her, then turned back again. But a second later, she turned back to look at him again. Chad saw her step back to stare with a look of surprise on her face. She was taking him in fully. He had to stand there and endure her looking at everything from his hair down to his shoes to the packages of diapers he was holding in his arms. He wanted to run, but it would do no good. Once again he wished the ground would just open up and swallow him.
He saw the woman searching for something to say. He wanted to say something to her first, apologize or something, but he held his silence. The man in front of the woman turned around briefly too. He too stared at Chad. Chad heard him utter a soft “shit” before he turned back around again. Chad’s sentiments exactly.
He sensed someone entering the line behind him. He was tempted to turn around and look, but he forced himself to stand still. The woman in front of him was still looking him over though. She was shaking her head now. “My day was bad enough and now I gotta’ run into this?” She shook her head again and turned away from him.
Chad wanted to apologize again, but now he realized that whoever was behind him was walking around to see what the woman in front of him had been looking at – which was him. It was a girl! “Oh my God!” the girl said as she covered her mouth with her hand and started laughing.
“What?” another feminine voice asked. The voice’s owner walked around to his other side to see what her friend was laughing at. Chad suddenly had two teenage girls giggling at him from both sides. Please earth, please open up and swallow me!
The giggling of the two girls caused the woman in front of him to turn around again and start giggling too. Chad wanted more than ever to drop the packages in his hand and run out. The man was paying for his purchases now, but he and everyone else were paying most of their attention to Chad. Chad felt so embarrassed. He wondered if the makeup on his face covered up how red it must be underneath.
The man finished paying and left. The woman in front of him stepped up to the counter and Chad took another step forward. “You’ve got gorgeous nails,” one of the girls still next to him said.
Chad swallowed hard. “Thanks,” he said softly, trying to ignore her as much as he could.
“Got a baby at home?” the other girl asked.
“No,” the first girl said before he could answer. “Those aren’t diapers for a baby. Look closer, they’re adult diapers.”
Chad was dismayed to see the two girls moving more and more in front of him so they could see him better.
“Your right!” the second girl replied. Then she looked up at Chad’s face. “For you?” she asked, and then went into another fit of giggling.
How could he answer that? He should have lied. He knew he should have. But instead of lying, he nodded his head ever so briefly and muttered, “Yeah.” The elephants rushing around through his insides were threatening to destroy him completely. The two girls broke out laughing harder than ever. Chad had no doubt now that his makeup couldn’t hide his red face.
“I wonder if he’s wearing a diaper now,” the second girl asked the first.
“Ask him,” the first girl suggested.
Chad’s embarrassment reached another whole new level as he saw the girl turn toward him again. “Are you wearing a diaper under your dress now?” And again she couldn’t contain her giggling.
Chad tried to look straight ahead and ignore her, but it was impossible. He was so embarrassed he wanted to cry. Instead of answering, all he could do was to nod his head again slightly. Both girls broke out laughing completely again, as did everyone else around including the woman behind the cash register. And that was when Chad realized that his chastity device was suddenly hurting him again. Damn! Damn! Damn! Not only did he hate his humiliating situation, he loved it too. Damn he needed some relief. He needed it bad!
The woman in front of him finally finished and moved out of the way. Chad stepped up to the counter and put his bags on top. The two girls stayed on either side of him, watching him closely and giggling. The woman behind the register had a broad smile on her face as she rang up the total and told him how much it was. He set his purse on the counter and fumbled with his nails to open it and dig out some cash. He knew he’d have to stop at the ATM and get more cash again later, but he hoped the cash would be quicker than a credit card. Besides, with the credit card he’d have to sign the receipt and just holding a pen was difficult.
“I am so jealous of those pretty nails,” the girl on his left said as he dug the money out.
“Me too,” the one on his right replied. “Maybe we should get ours done that long too.”
The girl on the left giggled again. “So are they glue on nails or what?” she asked Chad.
Chad really wanted to ignore her, but he handed the clerk his money and then turned toward the girl on his left. “Acrylic,” he replied softly.
The girl’s eyes went wide and she put her hand in front of her mouth as she giggled even more. “You must have really wanted those nails badly then,” she said through her giggling.
Chad accepted his change back from the clerk and dumped it into the bottom of his purse. He picked up his bags and started walking away. It had been so humiliating. More so than he could have ever imagined.
“Call me if you need help changing your diaper,” one of the girls called from behind him. He kept walking toward the door, doing his best to ignore them and everyone else. Teenage girls, they were always the worst!
He was ever so grateful to get back into his car and get away from there. He felt a lot safer in the semi-hidden security of his car. He could relax a little. As he drove down the road, he was more glad than ever now that he had decided to skip breakfast. His stomach still wasn’t calmed down from the drug store.
Since he really wanted and more probably needed a mirror, he decided to get everything else at Target. He just prayed that it would go easier than the drug store had. He pulled into the parking lot and breathed a little prayer for help, then he got out and walked boldly once again into the store. He grabbed a shopping cart and put his purse in the child’s seat. As he began walking, his eye noticed the women’s clothing section just ahead. He was very tempted to go over there and look around since he was dressed as a woman now, but he thought better of the idea and turned towards the rest of the store instead. It would be safer and a lot easier if he just got out of there as soon as possible.
Fortunately, the personal care items like shampoo and the razors were near the front of the store. He quickly found everything he needed, grabbing items and brands that were identical to what he was using now so he could spend less time looking through things. But he still needed pantyhose and a big mirror. Now where were they?
He remembered seeing the hosiery section out of the corner of his eye earlier and he headed straight for it. He needed to buy six pairs. He looked over what they had and selected six that were his favorites from what he had before, grabbing them in whatever shades that were available. But then he thought about the fact that he had ruined two pair just trying to put them on with his new nails this morning. Just to be on the safe side, he added two more pairs to his cart.
From there, he pushed his cart around through section after section of the store, searching for the mirrors. He noticed some people staring at him closely, but he finally realized that unless someone really looked at him, they seemed to be ignoring him. That was actually comforting – a bit. He finally found the mirrors in the very middle of the store. He selected a cheap one that could be hung on the back of a door and stuck it into his cart. Then he headed straight for the check out lanes.
For once, he only had to wait in line behind one other person and that wait wasn’t long at all. By the time he put all his things from his cart onto the conveyor belt to be rung up, there was only one other person behind him. The girl behind the register stared at him as he finished taking everything out of his cart. He pulled the cart all the way through and out of the way, then waited for the girl behind the register to ring up his purchases. But she was still just standing there staring at him as if she couldn’t believe what she was seeing. He saw the man waiting in line behind him staring, or rather glaring at him too. He just wanted to get out of there as soon as possible. The girl behind the register was making him a bit angry. “Would you please ring this up so I can leave,” he said. She finally started moving. He paid in cash again to make things quicker. Then he put everything he had just bought back in the cart to make it easier to get it all out to his car and got out of there as fast as he could.
As he loaded the mirror carefully into his back seat, he thought about what had just happened in the store. Yes, it had been very humiliating being in there and being stared at. But this time it had been a whole lot less humiliating. Partly because he had gotten a bit angry at the girl behind the register. Maybe he just needed an angrier attitude when he went into the stores. It didn’t exactly sound right, but if it would help…
Finally having everything he needed, he turned his car toward home again. He stopped along the way at a fast food place and went through the drive-through. He got no real reaction from the young boy at the window as he exchanged money, other than he saw the boy staring intently at his nails. Maybe the guy liked long nails on women.
He made one last stop before he went home. He stopped once again at the bank to withdraw more cash – a lot more cash. With his long nails, it was a lot easier to manage than signing for his credit card.

Sandy glanced once again at the object that was sitting on the passenger seat of her car. She had tried it herself back at the workshop. For something so simple, it really worked fairly well. Mostly anyway. The one big drawback that she now saw in it was that it was more of a torture device than she had thought it would be. But still, she hoped that Mel would approve.
She pulled into the parking lot in front of her apartment and started to get out of the car, then she stopped. No use taking it first to her apartment if she could deliver it to Mel now. She pulled out her cell phone and called.
“Hello?” Mel’s voice came over the phone.
“Hi Mel. It’s Sandy.”
“Hey Sandy. How are you today?”
“Great Mel. Listen. Remember that perch thing we had talked about for Sissy to stand on? Well, I’ve got it here. I was wondering if could bring it over now?”
Mel giggled into the phone. “Perch? I guess that’s as good a description as any. Sure Sandy, bring it right over. I can’t wait to see it.”
Sandy got out of her car and went around to the passenger side to grab the device better. It wasn’t all that big, but it was built fairly substantially so it was a bit heavier than it looked. She carried it straight up the stairs to Mel’s apartment. Mel had the door open and was waiting for her when she arrived.
“Hi Sandy,” Mel said as she walked up, but her eyes never left the object in Sandy’s hands. “Is that it?” she asked, fascinated to be looking at the thing.
“That’s it,” Sandy said as she handed it to Mel before she stepped into her apartment.
Mel turned it around in her hands to look at it better. It appeared to be made entirely from unfinished wood with a fairly heavy triangular base. Two wide boards stuck straight up from the base and supported a fairly thick round wooden piece between them. The side boards extended up another two inches from the top of the round piece. The more she looked at it, and the more she thought about it, the more the term “perch” sounded like the right description.
“Where’s Sissy?” Sandy asked.
“He’s off this morning. His car is gone so hopefully he’s out buying more diapers for himself.”
Sandy giggled. “I’m sure he must love doing that.”
Mel laughed. “More than that, he’s got no pants to wear so he’ll have to be doing it in a skirt today. And… wait till you see the new nail job he got last night.”
“Oh my God! I can’t wait to see him.”
Mel headed for the corner she usually had Chad standing in. “I gave him off till three today so he can get whatever personal business done that he needs to do.”
“Can I come back later then? I’d love to see how this thing works with him on it.”
“Of course,” Mel replied as she placed the device down on the corner of the floor. It fit perfectly into the corner. “But you may have to wait till a bit later though, I need to go out with him for a while as soon as he gets here.”
“Can you call me?” Sandy asked as she saw Mel looking carefully at the perch.
“You bet,” Mel replied, only half listening. She looked from the perch back up towards Sandy with a grin on her face. “Did you try it?”
Sandy giggled a bit. “Yeah. I think it works fairly well, mostly. But I’m also afraid it could be a real torture device.”
“I have no doubt,” Mel said, looking carefully at it again. She placed her hand against the wall and placed the heel of her left foot on top of the perch. She was wearing sneakers without a heel though so she wasn’t sure how it would work. As she put more and more of her weight on the device, she was glad to see that it seemed to be sturdy enough and that it wasn’t going to slip out from under her. She quickly shifted her weight and brought her right foot up onto the thing too. The tight confines of the bar her heels were resting on kept her feet close together. Her balance immediately shifted onto her toes since she wasn’t wearing any regular heels and she immediately noticed that it also seemed to force the rest of her body into the corner. The height of the bar did keep all her weight onto her toes though since she didn’t have any heels and she could tell that it could get very tiring, very quickly. “Damn,” she said as she tried to move her feet a little. “Even with sneakers on I can’t move my feet much. And it pushes me further into the wall.” Very carefully, she lifted one foot straight up off of the thing and stepped away so she could get her other foot off.
Sandy was a bit worried about what Mel might really think of the device. “Well, what do you think?” she asked. “Too dangerous?”
Mel smiled. “Are you kidding? I think it’s going to be great,” she replied as she turned and walked off.
“Where are you going?” Sandy asked.
“To get some shoes with a heel!”
Mel came back a minute later wearing her four inch patent pumps. “Now those are killer heels!” Sandy declared.
Mel laughed and once again placed her left foot carefully on the perch. With the heel over the bar her foot felt like it was more locked into place. She noticed that even with four inch heels on, the bottom of her heel was still up a good half inch from the base of the device. She shifted her weight and quickly brought her other foot up again too. Once again she was pushed into the wall, but not quite so bad now.
She tried to move her feet and found that any movement, side to side, or front to back was now totally denied. She could only lift her feet straight up and off of the thing. Her weight was better distributed too since the bar now held half her weight and her toes the rest. The thing would still be painful, but not nearly so bad. “This is great!” she declared as she pried herself off of the thing. “I can’t wait to try it on him later. Who would have ever thought that something so simple looking could work so well.”
Sandy felt elated. “So it’s good then?”
“It’s great, Sandy. It’s great!”
“Good. I’m so relieved.”
“Why? You always do good stuff and if this didn’t work out then it wouldn’t really matter.”
“Well. I wanted it to work out because I want to ask you a favor.”
“A favor? Sure anything. What is it?”
“I want to babysit with Sissy again.’
Mel laughed. “Oh, I think that can be arranged.” But as soon as she said it, she remembered the pictures from the last babysitting session that had gone on – and she remembered hearing about the things that the pictures hadn’t shown. She had just agreed, but at the same time, she was having some misgivings now. But unfortunately, she had already said yes. She’d just have to hope that things went ok next time.
Sandy was all smiles though. “Oh Mel, thanks so much. Listen, for next time, I’ve been studying some videos for something I want to do…

Tuesday, April 27, 2010

The Bet - Chapter 22 (Saturday – week 3 Part 1 of 6)

The Bet
by Karen Singer

Chapter 22 (Saturday – week 3 Part 1 of 6)

In the early morning hours, before it even began to get light, and long before she even started to become awake, she dreamed of a house. Her house. Her perfect, beautiful house. A house that everyone loved and envied her for. A house with a stone exterior set on acres of beautifully manicured grounds. The interior was furnished in a mixture of new things mixed with the things she had loved and saved from her parent’s home. Things that meant so much to her.
In her dream, she wandered through her house and touched those pieces that were special to her. Each touch brought her feelings of love and joy – as did Sissy, who stood quietly in the background, always awaiting her slightest wish.
She had dreamed about this house often, but this time, her dream was far more detailed, far more complete than it had ever been before. And it was so real that even in her sleep, she could almost touch it, smell it, have it.
Happily, she drifted out of the dream into a deep sleep once again, till hours later, she woke up feeling happy and fulfilled, still remembering odd remnants of her previous dream. A dream she wanted badly just then, just like she wanted some coffee!

No loud music blared into the room when Chad woke up. The full light of the sun seeped all around his shades, startling him for a moment before he remembered that it was Saturday. The weekend. No work – at least not for the company. Mel was another story.
He pried himself out of bed and looked at his pink clock radio. It was later than he thought. He stretched and yawned happily around the pacifier that was still in his mouth. It was good to get some extra sleep once in a while.
He fanned his fingers out on both hands and looked at his new nails. Huge claws. How was he supposed to live with them? He grabbed one of the nails and tugged on it. It seemed strong enough, yet it felt fragile too. Strange.
He waddled in his wet, messy diapers out to the kitchen and read the note Mel had left on his counter, his long red nails catching his eyes as much as the words on the paper.


It’s Saturday. You have the day off till three o’clock. Don’t be late!
While you’re off I expect you to make the most of your free time. You need at least two more packages of diapers and at least six more pairs of pantyhose. And make sure you stock up on anything else you’re running out of. This is your time to take care of those things. Don’t you dare buy anything for yourself that might be even partially thought of as masculine or I will punish you severely!

When you arrive at three, I expect you to be in a perfectly pressed uniform. I will inspect!

Don’t call me for anything before you arrive. The day is yours.

Chad read the note three times and finally sighed deeply. Another day off. He distinctly remembered last Saturday. What a pain that day had been. He had no doubt that today would be equally as bad. His mind quickly made note of two distinct things that made him panic slightly – first, he had no pants to wear so he would be in a skirt when he went out shopping, and the second thing was that he would be going out shopping with his super long red fingernails.
He placed his hand on the kitchen counter and pressed down with just his nails, as if testing their strength, trying to pop them up. They seemed strong enough, too strong maybe.
He waddled over to the refrigerator and pulled out one of the few bottles of tea that was still in there. It would be nice if he ran out and she didn’t replace them. He knew better though. He grabbed one because he wanted one and had nothing else to drink. He finally removed the pacifier that he had slept with all night and headed into his living room. He sat in the only chair he owned and stared at his blank walls while he nursed on his bottle and thought about his morning ahead.
He had to go shopping again. He needed to restock his supplies. Seemingly normal stuff. The problem was leaving the comfort of his apartment while dressed the way he knew he’d have to be. There would be no trying to hide anything today - not like last week. He quickly figured that things would undoubtedly go easier for him if he tried to look as much like a woman as possible. He hated the idea. He hated the idea even more because it added heaping amounts of fuel to his already over stimulated and under-relieved sexual need.
Damn. Was he really doing this? Was he really about to go out shopping dressed entirely as a woman again – only this time by himself? Unbelievably, the answer was yes. He never dreamed he could ever go out like he had been – or like he would be doing shortly. Never – ever – dreamed! Yet he was doing it. And dare he think it, loving it? Because way deep down, he really was living his fantasies. Damn he needed some relief!

Mel opened the larger of the two boxes that had been delivered yesterday. She removed the dress from the packaging and crammed it into her closet next to the one that had arrived before. Both of them had super-full skirts. Neither of them really fit in the closet and with both of them there, they took up way too much space. But she had no other place to hang them and she didn’t want to send them to Sissy’s apartment yet. In fact she didn’t even want him to know about the new dress yet. That was for later. So she just crammed both dresses together as best as she could. The shoes and the anklet socks she put in the closet on the floor. There wasn’t much room for them either.
She really needed a bigger closet. Thoughts of the house she wanted invaded her mind again. A really huge closet would be so nice. Just as soon as she had won this bet she would buy a house. With Sissy there to take care of it, she would have no worries. She wondered again if he realized yet that he had already lost. Maybe she should talk to a real-estate broker now and get things rolling. That was a pleasant thought. But no, it was still too soon. There was no need to rush things.
She finally turned to the smaller of the boxes that had arrived, his breast forms. She opened the box and pulled one out. It felt soft and a bit squishy… and all too real. It was also heavier than she expected. But then, weren’t her own breasts heavy? She smiled, her breasts might be heavy, but she lived with them and loved them. And she wouldn’t have it any other way. Now Chad could experience the same wonderful feeling too. Although she wasn’t really sure how wonderful he would feel about it. But then it was hard to tell, he was a sissy after all.
She put the breast form back into the box and pulled out the little spray can of glue. Would it really hold that well? She’d just have to see. She put the can back into the box and pulled out the printed instructions. One thing caught her eye that she hadn’t thought of before, the glue needed another product to soften it for removal. She hadn’t bought any. She’d have to look around in the stores to see if she could find some. She put the whole box into her closet and out of the way where he wouldn’t see it. The breast forms, like the new dress, were for later.
She wondered how he was getting along with his new nails and almost laughed. She knew how impossible nails half that length could be. She had no doubts that he was finding his situation interesting… to say the least. Between thinking about his new dress and the breast forms and him having to deal with those extra long nails, she was quickly becoming moist and sexually charged again. Tonight! Tonight for sure!

Chad stared at his closet. He had just finished hanging everything back up that had been on the floor, but his closet still looked empty. Seeing only feminine clothes in there now and no male clothing at all was both thrilling, and frightening. And if Mel had her way, he figured his collection of feminine things would be growing drastically. Which he wasn’t totally opposed to, he did like wearing them after all. He always had. He just didn’t want to do it permanently. But if he didn’t win this bet, then that’s just what might happen and the thought of it scared him. Fortunately, he was completely back on track again to win, and hopefully there would be no more episodes like he experienced yesterday. That had been troubling. But he was already doing much better than yesterday. His best time so far today was already up to sixteen minutes, a far cry from his best time of eleven minutes yesterday. But then yesterday had been weird. He was more determined now than ever to win this bet – no matter what! Self-respect, friends, and a life!
He had already showered and put on two fresh diapers. His girdle was already in place as were his pantyhose – although he almost left the pantyhose off completely. Putting them on with his super-long nails had been almost impossible. Just trying to roll them up with his nails had been impossible - he had ruined the first two pairs he tried to put on in the process, and if he had to wear a dress today then he couldn’t wear pantyhose with runs in them.
His makeup and hair were also done. His nails had been a major hindrance there too. He couldn’t believe how difficult it was to just open the eye shadow container. Major difficult. And try to pick up something tiny? Forget it!
More and more he found himself moving his fingers strangely because of the claws on his fingers. And because of it, he thought the end result was that he was having to move his hands more femininely. Not because he really wanted to, but because the nails were forcing him to. It was not only humiliating, but every little movement of his fingers now reminded him of his feminized predicament – and constantly refueled his huge sexual need. A need so great now that he wanted to make a fist and punch the walls… but of course, the nails wouldn’t even let him make a fist.
With his clothes finally hung up, it was time to get dressed. But what should he wear? He didn’t have another complete skirt and top set like he had worn yesterday. Without removing anything from the hanger this time, he sorted through item after item and looked at his choices carefully. Finally, he chose a dress that he had owned from long before he met Mel. He had always liked the dress and he thought he looked good in it – he hoped anyway. The simple dress was of a dark solid material that he hoped wouldn’t stand out too much, and it was belted in the middle which he hoped would make him look like he had more of a figure than he had. Perfect.
He padded the bra-part of his girdle with the two pairs of pantyhose that he had ruined earlier and slipped the dress on. But zipping it up the back with his long nails was nearly impossible! He twisted the dress this way and that as he struggled to grab the zipper with enough force to pull it all the way up. But finally he got it there. He wasn’t looking forward to having to unzip it again later.
With the belt finally fastened, he looked at all the shoes in his closet. He decided not to wear the low heeled pumps that went with his maid’s uniform. They would have been the most comfortable, but he didn’t think they would go as well with his dress as some of the others he had. He chose the most medium height heels he could and buckled them on, hoping that they went well enough with his dress.
He easily slipped his ring over his long nail and onto his finger, but his necklace and watch were almost impossible to fasten. He almost gave up on the necklace before he finally got it. The watch was only a little easier.
Not being able to see himself fully since he didn’t have a full length mirror, he checked what he could see in the bathroom mirror. He hoped it would be good enough because he really didn’t know what else he could do.
He found his pen and some paper and stated making a shopping list. Diapers, and pantyhose went on first. But trying to write them almost made him give up on creating the list. Just figuring out how to hold his pen with the nails he had now was difficult. Once he had written those first two items, he added razors and some more of the moisturizer that he used instead of shaving cream. He also added shampoo and conditioner and deodorant. He checked his makeup supply and decided that he was ok for now – thankfully. Finally, he added a full-length mirror to his list. The way things had turned now, he figured he needed it. And it would be interesting, if not helpful, to see how he looked whenever he got dressed.
He had a lot to do and it was time to get going… like it or not. He grabbed his purse and stopped for a moment and stared at his door. He took a deep breath for courage and finally opened his door and headed out. Just walking down to his car was nerve-wracking. But surprisingly, wearing the dress along with his new fingernails, he felt rather more feminine than ever. He was scared to death, but deep down he was enjoying it too.
His nails made him fumble with his purse as he tried to fish out his car keys, then they made him fumble more as he unlocked his car. In fact, they were making him fumble with everything. In reality, the nails were simply impossible! He had seen nails that long on a few women before, how did they get through life? He couldn’t even grip his steering wheel the way he usually did because of the nails, they were in the way of everything.

Friday, April 23, 2010

The Bet - Chapter 21 (Friday – week 3 Part 4 of 4)

The Bet
by Karen Singer

Chapter 21 (Friday – week 3 Part 4 of 4)

As per Mel’s text reminder, Chad hurried home after work and cleaned himself up quickly. It was Friday night, their usual night to have their nails done. He was surprised at how normal the routine seemed to him now. He dreaded it, yet it still seemed normal. He just hoped that this time the color would be a bit better than the electric pink that his nails were now, yet how odd that he had somehow gotten used to the bright color too.
As per her usual instructions, when he got dressed again, he left his pantyhose off. His bare legs looked all too pale and white in their naked state. Not nearly as good as they had looked before – he thought so anyway. He had been incredibly conscious of his exposed legs all day in the skirt. He had been horrified to have to wear it, yet deep down, he was excited by his situation too. His bare legs now felt so different against the colorful material of the skirt as it constantly moved around him. Where the pantyhose had accented some feelings, they had also muted others. Now, those muted sensations seemed all too prevalent – and sensual. He was thankful that he had shaved his legs so well that morning.
Once he was ready to go again, he glanced at the pile of clothes he had left on his bedroom floor from earlier that morning. Mel wasn’t there yet, so he picked up a dress that was on top of the stack and opened his closet door to get a hanger – and stopped dead. The first thing that he noticed was how much extra empty space his closet now had. The second thing that caught his eye was all the empty hangers that used to hold his male shirts. And the last thing that he noticed was that there was nothing in the closet at all that was wrapped up in Mel’s cling wrap. It was all gone – missing. Every piece of male clothing that had been in there was totally gone! Vanished! He stared at his empty closet in complete disbelief.
There was a quick knock on his door, but he didn’t move. He soon heard Mel using her key to open the door. “Sissy? Are you ready?” he heard her calling.
He turned toward her, still standing at the entrance to his closet, but he was still too much in shock to answer her.
“Sissy?” Mel called again as she walked quickly toward his bedroom. She found him there, with his mouth open in surprise, standing in front of his closet. She smiled as she realized what his problem was. “Come on now Sissy. We don’t have time for you to waste, gawking at nothing.”
“But…” Chad got out and pointed at his closet.
“Yes, I know,” she replied, “it’s all gone. Now get a move on so we won’t be late.”
As if in a dream, Chad dropped the dress that was in his hands back onto the pile on the floor and followed her out toward the door. Mel handed him his purse and diaper bag and led the way out. “Hurry up, stop dawdling!” she commanded, trying to get him to move faster.
Chad moved faster, but only a little as he followed her down the stairs and got into her car. “My clothes…” he started to say as Mel took off like a racecar driver from the parking lot.
“Yes, I know, they’re gone now,” Mel replied simply as she raced down the street.
“But you don’t need them anymore.”
Chad wanted to protest, he wanted to argue, but there was nothing really to protest or argue about. “What did you do with them?” he finally asked.
“I put them somewhere where we both will have trouble getting at them.”
“So you won’t be thinking about them anymore. You don’t need them anymore. You’ve turned another corner, Sissy. It’s time to continue down the avenue.”
Chad wasn’t all that sure about her metaphor, or what she really meant, so he said nothing.
“So, how was your day?” she asked happily.
“Ugh!” he grunted. “One of the worst!”
Mel smiled delightedly. “Because of your little accident at the gym?”
“Oh God!” he replied. “That was awful! But it’s more than that. My whole day was terrible.”
“Why, because you had to wear a skirt today?”
He didn’t even have to think much about that one. “Definitely!”
“What do you mean?”
“Well, in some ways I guess I didn’t have a problem. I guess because I’ve been dressing too much as a woman already.”
“Too much? Not at all.”
He didn’t reply to that. “But in other ways, the skirt caused me nothing but problems!”
“Ok. So tell me.”
“Well, the worst of it was all the women at work. Geez! Would you believe they told me they had been taking bets on when I would start wearing skirts?”
Mel laughed. “I’ll bet they were. Did anybody win?”
“I don’t know and I don’t care.”
“But that wasn’t really the bad thing. This afternoon they all descended on me in a mob and dragged me down to the break room with them.”
Mel laughed again. “So they kidnapped you?”
“Yeah! Exactly.”
Mel was really enjoying hearing about it. “And they took you to the break room? Why?”
“To humiliate me! What else? The kept making comments like, ‘you have good legs,’ or ‘I like your outfit.’ Then they made me sit down and wanted me tell them all about why I’m doing this.”
“So did you tell them?”
“Not on your life! No way!”
“Why not?”
“Don’t be ridiculous! I’m not going to tell them anything at all about this bet!”
Mel laughed again. “So what did you do?”
“I finally escaped and got out of there.”
Mel was delighted hearing about it all. But the only reply she could make just then was to teasingly say, “You really do have pretty good legs.”

The same nail technician was waiting for him when they walked into the salon. Before he could even say hi to her though, she was motioning him to follow her to the back. “Hurry up, we’ve got lots to do today,” she said, trying to get him to move a bit faster. “You look pretty today,” she said as he sat down in the chair to have his toenails done.
He wasn’t sure what to say, so he just said, “Thank you.”
“I like your hair that way,” she said as she unbuckled his shoes and slipped them off.
“That seems to be the general consensus,” Chad replied.
Chad was now familiar and comfortable with the procedures for having his toenails done and he sat back and relaxed while the technician did her job. He was happy to see a pretty red color being applied to his nails a few minutes later. It was certainly a lot better than the pink they had used on him last week.
A little while later, the technician led him over to a table where she started working on his fingernails. She seemed to be spending a lot more time cleaning them this week than she had before, then she began scuffing them up instead of polishing them. He was really surprised when she began gluing very long extensions onto the very tips of his nails. The plastic extensions had to be at least two inches long, and she had glued them onto the very edge of his nails. “What are you doing?” he asked as a wave of panic raced through him.
“Making your nails look better,” the nail technician replied. “You cut them last week. This week, Mel asked that we fix them.”
“But they’re so long!” Chad complained.
“Don’t worry, I still have to cut them back.”
Chad could only sit still and watch as she finished gluing the long claw-like extensions onto all his fingers before she finally cut them, but still leaving them horribly long. Then she began mixing some kind of glop that she used to fill in on top of his nails, and then over the new plastic nails, making them all look like natural, very long fingernails. It was a fascinating process. It just would have been a lot more fascinating if it were being done to somebody else. She was giving him long fingernails! Very long fingernails! The very sight of them panicked him again. Yet that panic also fueled his all too unrelieved sexual need. He had long feminine nails! Oh no! How horrible! And his chastity device began biting because it excited him so much.
He was glad when she picked up her file and began filing them, but all she did was to shape them better and not really shorten them at all. Finally, after what seemed like an eternity, she began applying the color, and a little while later, his fingernails matched his toenails.
He held his hands up and wiggled his fingers. So feminine looking! He tried to make a fist with them, but he couldn’t even get close. He had no doubt at all that the nails were about to make his life a whole lot more difficult.
This time, Mel had been finished long before he was and was waiting for him up front. “Let me see,” she said excitedly. He shyly held his hands out to show her. He heard a lot of giggling from the other women who were sitting in the waiting area, but he ignored them as best as he could. “Oooohhh,” Mel cooed. “They look so pretty now.” Then she giggled.
“But they’re so long,” Chad complained.
“That’s right!” Mel replied. “Next time, don’t cut your fingernails! Maybe this will help to remind you!”
Chad had no doubt that he was thoroughly stuck with the awesome looking claws now. The job was done and there would be no removing them for a while.
“Pay for your nails now Sissy so we can get some dinner.”
Chad dutifully went up to the cash register where the nail technician was waiting for him. The moment he started opening his purse was the moment that he really noticed the difference in his nails. They felt so strange as they got in the way. And when he dug out his wallet, the nails were even more of a hindrance. Handling the bills wasn’t too bad as he paid the woman, but he was very glad that he didn’t have to deal with any coins. He had a feeling that coins would have been impossible.

Mel drove them directly to a nice restaurant for dinner, one that he hadn’t been in before. The night before, Mel hadn’t made him use a baby bottle to drink from, but he had no illusions about being so lucky tonight. His whole day had been a disaster so far, so he wasn’t the least surprised when Mel pulled an empty bottle out and set it on the table even before they had ordered their drinks. She set the bottle off to the side of the table, but it was never out of Chad’s view.
When the waitress asked for their drink order, Mel asked him if he wanted coffee again. With another glance at the bottle, he shrugged his shoulders and agreed. The bottle would be hot to hold, but hopefully not too hot.
Mel saw him glance at the bottle and smiled. Then she began talking. “I remember back when I was in High School. I did a lot of babysitting then. It was fun and I loved making my own money. Did you ever do much babysitting?”
Chad was surprised at the question but replied that he had done some, but not a lot. Mel listened, then kept talking about her life back then and Chad mostly listened. Occasionally they compared experiences. Sometimes they laughed. And when the waitress finally brought their coffee, Chad again waited for Mel to pour it into the bottle on the table, but she never did. So eventually he picked up the cup, clumsily with his new fingernails, and began sipping from it.
It was another really pleasant meal filled with nice conversation. Mel told him quite a bit about her early life and he told her a little bit about his. He was surprised to find out that she came from a fairly well to do family. She wasn’t the least bit surprised to find that his upbringing was more middle class. But while her mother and father had been killed in a car accident a few years ago, he had only lost his mother. And although his father was still alive, he hadn’t seen him now in many years and didn’t even know where he was. His father had never been around all that much while he was growing up anyway, so he really didn’t even miss him. Mel found that to be terrible. She still missed both her parents desperately.
When dinner arrived, Chad had to deal with learning to hold his utensils with the longer nails. It was a major inconvenience, but nothing that he couldn’t manage and he didn’t even mention it while they continued to talk all through their dinner. Their conversation lasted a long time and they were really just enjoying each other’s company, no longer thinking about the way they lived outside of the restaurant.
By the time the waitress cleared away their empty plates, Chad didn’t even remember how many cups of coffee he had finished. He did know however that it was enough that he had wet himself twice before they got up to leave. He never bothered to time himself on holding back though. He had just held it a little then gave up. It was too much trouble to do anything else – under the circumstances.
The meal had been so pleasant that he felt sorry when they finally left. He watched Mel pick up the unused baby bottle and put it back in her purse. He was glad that she had decided to not make him use it. But the sight of it had kept him worried about it all during dinner. But just the act of getting up from the table and walking out brought back all the strangeness of his new life. The feel of his skirt on his bare legs and the weight of his purse on his arm left him no doubt that things were back to normal again. Dinner was unfortunately over.
On the way back to Mel’s apartment in the car, Chad remembered something important. “Mistress, I need to get some laundry done – badly. Can I start some when we get back?”
Mel shook her head. “No, Sissy. I’ve decided that from now on you can only do your laundry on the weekends. My things I may have you do anytime, but your clothes will have to wait till the weekend.”
He wasn’t exactly happy to hear that. “Why?” he asked.
“Because that’s the way I want it.”
Chad was quick to realize the implications of that. Since he only owned four pairs of slacks, that meant that there would be three days each week when he would be forced to wear skirts and there would be no way to avoid wearing them to work again. Not exactly a situation to make him happy. Yet, at the same time, he found his latest predicament sexually thrilling too. If only he could get some relief!
When they got back to Mel’s apartment, she had him carry another big box from her trunk up to her apartment along with a smaller box. After what had been in the box he had carried in last night, he was a bit afraid of her opening either of these boxes. But Mel just had him put them in the corner of her room and didn’t mention them again. And after last night, Chad was glad.
Mel seriously considered tying him up, blindfolding him, then using him again for her own sexual pleasure, but she decided against it. Not tonight. Not after the wonderful conversation they had both just enjoyed during dinner – a dinner that had lasted a surprisingly long time. For a sissy, the guy could be interesting to talk to. And for once, it was nice to have someone who was interested in hearing about her interests. So nice.
She finally decided to just send him home early. So she sat him down on the floor to drink one last baby bottle of her tea, then she removed his diapers and cleaned him up. She stuck another suppository up inside of him and rediapered him for the night. Then she took him home dressed just like that. She helped him into his baby-doll nighty and helped lay him down on his blow-up mattress. She got him two more bottles to drink and put his pacifier down next to him. She leaned over and kissed his forehead as he suckled on the first bottle. “Good night, Sissy. Sleep tight.”
She stopped at the door to his bedroom and turned out the light. She glanced back at him, still sucking on the bottle. She could just see him in the dim light that filtered around the shades on his window. She was making progress with him, good progress. She wondered if he even cared that he was losing this bet already. She turned away and left him. She would be back much later after he was asleep to leave him a few instructions for tomorrow. Tomorrow was going to be a busy day. She had big plans.

Chad sucked on his bottle while he watched her leave. He had really enjoyed dinner again. Not just the food, but mostly, just being with her. It was such a shame that he wasn’t the kind of person she would ever seriously consider going out with – especially now that she knew him so well. Such a shame.
He thought about her as he finished the first bottle, and all through his second one. And when he finally finished it, he put it down on the floor next to him. His eyes caught sight of the pacifier she had placed near him. He felt a strong desire to pick it up and suck on it, but he fought the urge. He rolled over instead and tried to go to sleep. A little while later, he woke up when something fairly hard and sharp scraped against his tongue and the roof of his mouth. He was surprised to find that he was sucking his thumb and the long nail on his thumb was in the way. Irritated, he pulled his thumb out. He opened his eyes and spied the pacifier on the floor. No, he didn’t want to suck on it… yes he did… no he shouldn’t. But what could it hurt? He reached out and picked it up awkwardly around his extra long nails. He put it into his mouth and sucked on it. Instantly he felt a wave of calming pleasure as he had been hypnotically programmed to do. He fell asleep, and dreamed of wetting his diapers.

Tuesday, April 20, 2010

The Bet - Chapter 21 (Friday – week 3 Part 3 of 4)

The Bet
by Karen Singer

Chapter 21 (Friday – week 3 Part 3 of 4)

Robin finished her lunch and drove back to work. As she passed Chad’s cubicle, she noticed that he wasn’t back from lunch yet, but then she was a bit early. All through lunch, she thought about what had happened at the gym. Not much really. What had she really learned? Again, not much. She had wanted to ask that trainer that he was visiting – Cassie – more about what she was doing with him, but she just couldn’t work it into any of the conversations. Mostly, Cassie had just touted how good the gym was – which did really sound great… and worse, she knew how much she needed it. But she knew that she would never be joining. Not only was it expensive, she was just too lazy.
No, she hadn’t gotten all that much out of her visit at all, except maybe one thing. And she was going to use it as a major hammering stake with Chad!

Mel had just parked her car when her cell phone went off. “Hello,” she said quickly.
“Hi Mel,” Cassie’s voice came over the connection.
“Hi Cassie. How did it go today?”
Cassie started laughing. “Oh Mel, you wouldn’t believe it. I was just rubbing some baby lotion onto the front of him, not really doing much else yet, when he started peeing all over the place… and he couldn’t stop it!”
Mel was shocked. “He couldn’t?”
“No! Not at all. I have to tell you, he was really upset about it. And let me tell you, it went everywhere! Quite a mess!”
Mel laughed, “I can imagine. I’m sorry about that. Do you need to quit taking care of him?”
This time it was Cassie’s turn to laugh. “Are you kidding? I’m loving this. You wouldn’t believe how fascinating all this is.”
Suddenly, Mel wasn’t all that happy with Cassie taking care of Sissy for her. She felt jealous because Cassie was discovering things that she herself never got to see. But the end result was that she had far more proof now that she was winning the bet. Her confidence soared. There would be plenty of time later to see things for herself. The bet was all that really mattered. “I’m just glad you’re helping,” she replied.
“Hey, did you know he came in today with another woman from work? Someone named Robin.”
“Robin? She was there?”
“Yeah, I gave her that ten cent tour. I’m pretty sure she’s not at all interested in joining the gym though.”
Mel was fairly sure too. She didn’t know Robin but she could just imagine. She was probably young and really good looking, the type that didn’t need the services of the gym. She felt the strings of jealousy once again trying to get at her, but she pushed them away. “Ok, Cassie. That’s good to know. I appreciate it.”
Mel put her cell phone away and went into the store where she bought two fairly large packing boxes and some packaging tape. She put them into the trunk of her car and drove home. She didn’t go to her apartment though, she went directly into Chad’s. She put everything she had gathered up earlier that morning into the two boxes and sealed them up completely. Then she dragged the boxes down the stairs and lifted the heavy boxes into her car. One box went into her trunk, but the other one had to go into her back seat. Then she drove to the storage unit that she had rented several years ago. She unloaded the boxes from her car and dragged them into the unit where she had some other things stored.
When the boxes were inside, she looked carefully at all the beautiful furniture and things that she could see from where she stood outside. Most of it was packed away carefully in boxes. Most of it had belonged to her parents before they died. It was all things she didn’t want to part with. But she wasn’t ready to commit herself to owning a big enough house to hold it all – yet.
As she drove back to work, she thought about Chad. He had no male clothes left to wear, only female. Little by little she was stripping his male existence away from him – completely. And he was about to discover that he would be leading a more and more feminine life as this bet went on.
She had previously denied him the ability to do anything more than to just pee out of his male appendage. Denying him totally. Now she would be denying him any kind of male existence at all – more and more anyway. Denying him – and fulfilling her! The thought actually sent waves of pleasure throughout her. She was surprised to find herself getting a little bit wet in her private regions over it. She didn’t know why she liked it so much, but she did. And since she could, she was going to take as much advantage of that as she could.
The denying him thoughts reminded her of the one little problem she had been nursing in the back of her mind for the last few days. She had given him mixed signals. That had been a big mistake. With a suddenly realization of what she had to do, she smiled with new confidence. She knew what she wanted to do with him now – completely. And what was better, she now had proof that she was winning this bet. He was going to be hers for a very… long… time!

Chad brooded all afternoon about what had happened with Cassie and why he couldn’t find those muscles to control himself. He stared at the project on his screen, but he got no work done because of it.
A little while after lunch, the suppository that Cassie had stuck up inside of him began to do its thing, just as it usually did about that time of day. The discomfort from it made him twitch and strain a bit. There was no fighting it, and he really didn’t even try, but in the middle of messing himself, he suddenly realized that he could feel those muscles again. As the mess continued to come out of him in tiny bits at a time, he now experimented with tightening his muscles. As before, they didn’t really want to react at first, but as he tried it over and over again, he felt more and more elated. The suppository had finished doing it’s job, which wasn’t all that bad since he had again had a very light lunch, but more importantly, the suppository had somehow kick-started his muscles again. He was back! He knew it, and he was going to win this bet!
Feeling much more confident, he squirmed to settle the mess in his bottom more comfortably and got to work, but the words ‘self-respect, friends, and get a life,’ kept going through his head.

Mel came out of the conference room and shook hands again with her client. She watched till he was out the door. “What’s next?” she asked Andrea.
“Nothing for another hour,” Andrea replied. “But another package came for you a few minutes ago. This one is smaller though.”
Mel was curious. “Smaller?” She walked over to Andrea’s desk and found the package. It was a little bigger than a shoebox, but she didn’t remember ordering him another pair of shoes. But then she didn’t remember anything that she had ordered for him. She was way too drunk that night. “Scissors?” she said as she stood over the box on Andrea’s desk.
Andrea handed her the scissors and Mel opened the box. She removed the lid and looked inside. She was shocked… deeply shocked. She reached into the box and touched one of the objects inside. Even through the plastic it felt a bit weird. She felt a bit dirty just touching it. But then she laughed.
“What is it?” Andrea asked. Mel tilted the box to show her. “Oh my God! Are they what I think they are?”
Instead of answering, Mel pulled out a piece of paper from the box. Something else in the box caught her eye. She picked it up and stared at it in wonderment. A small spray can of surgical glue. She looked briefly at the paper. Instructions. She handed the paper to Andrea.
“Oh… my… God! Oh… my… God!” It was all that Andrea could say.
Mel watched as Andrea looked back up at her. Then both of them cracked up laughing. Chad’s new breast forms had arrived, and she couldn’t wait to see them on him.

Robin was watching the clock. She had purposely been avoiding Chad all afternoon, leaving him alone. But not for much longer. It was now a little before her break time. It was now or never. With a feeling of excitement – and purpose, she walked around to his cubicle. “Hi,” she said as she walked in.
Chad turned around in his seat. “Hi Robin,” he replied, knowing she was probably heading down to the break room and would be asking him to go again. But she walked into his cubicle instead and leaned up against his desk.
“Maybe I should have said, “Hi Sissy. Would that have been more correct?”
Chad suddenly wanted to scream. He shook his head. “Robin, please…”
“Please what?” she asked. “Please call you Sissy instead?”
“No! Please don’t!”
“Why not? That’s what your other friends call you at the gym. Why should I be any different?”
How could he answer that? “No… it’s just that… that’s different.”
“What’s different? You mean I’m not your friend? Whether you like it or not, I like to think I am.”
“Yes, you are my friend. The only friend I think I have left now.”
“So why won’t you tell me anything then? Why do they get to call you Sissy and I don’t? By the way, it is a better name for you now.”
Chad felt so frustrated. “Robin, please…” but he didn’t really know what else to say. “It’s just complicated.”
“Well then, Sissy, why don’t you uncomplicated it for me?”
“I can’t!” he replied turning himself back away from her so he wouldn’t have to face her.
She had tried. But she was only really starting. There was a lot more to do now. “I don’t believe you for a minute – Sissy! But I’m going to take my break now, are you sure you don’t want to come with me?”
“No!” he said, not bothering to turn around. “And please stop calling me Sissy.”
“No!” she replied purposefully.
He turned back around horrified. “Why not?”
She smiled at him wickedly. “Because… it’s complicated!” She left him then and headed straight to the break room. It felt good to leave him with a taste of his own medicine. But if her friends were still up for it, she’d be seeing him for round two very shortly.

Chad was upset. Now Robin was calling him Sissy. And he knew that the way he had treated her was only making her more likely to keep calling him that. A thought struck him, she wouldn’t actually tell anyone else, would she? She was his friend after all. But that didn’t really mean all that much.
Ten minutes later, he heard a lot of noise out in the hallway, a bunch of voices all talking excitedly, and the noise was getting closer. Curious, he backed his chair up into the entrance to his cubicle to see what was going on. Robin and a ton of her friends were heading straight for him!
“There he is!” he heard one of the women shout excitedly.
“You mean there SHE is,” another woman corrected her.
Chad was petrified as he suddenly found his cubicle invaded by not just Robin but all too many of the women from around the company. He backed his chair up as far as it would go, but his cubicle was soon full of feminine voices surrounding him.
“What’s going on?” he demanded.
“Well… Sissy…” Robin explained, “we decided that you’ve been keeping to yourself way too long now. You need to get out more and talk to some other people. And who better to talk to than us. So we’re taking you to break with us.”
“No! I don’t want to go to break!” Chad replied quickly.
“Tough, Sissy, because you’re going!” With that, Robin grabbed his left arm and another woman grabbed his right arm and together they dragged him out of his chair towards the entrance to his cubicle.
“No!” he screamed again, pleading with them to stop. But they didn’t stop. The women never once let go of him all the way to the break room.
“He does have pretty good legs,” he heard one of them remarking as he was being led along.
“I like his outfit,” another one remarked.
“I like his shoes,” still anther one said.
“Where do you get your hair done,” still another one asked.
“His nails are sooo pretty,” another one remarked.
Chad was going crazy. He was surrounded by women who were determined to make his life miserable – again. And they weren’t giving him any way out. They led him, noisily, all the way to the break room, then straight to a big table in the middle of the room.
“Have a seat, Honey,” one of the women said as she held out a chair for him. Chad found himself almost pushed into the chair. He sat down and stared at all the women taking seats around him. All around him. Still leaving him no way to get out.
“How do you take your coffee?” one of the women asked.
“She likes it black,” Robin replied for him.
He looked at her. She was smiling evilly at him. All the women in his life now smiled evilly at him. All of them… and all too often. “What do you want?” he asked.
“Just to talk,” Robin answered simply. Then she walked away to get herself a cup of coffee.
Someone set a cup of black coffee in front of him and he picked it up. Tentatively, like it might be poisoned, he took a sip. But coffee wasn’t going to do anything to calm his nerves now. He thought about the nipples on his bottles and suddenly craved one.
“So Sissy,” one of the women asked, “why have you been keeping yourself from us?”
Chad shook his head. The crazy woman was serious! “Uh, I didn’t want to upset or disturb you,” he replied, trying to be nice.
“Oh don’t be silly. You’re not going to upset us? We LOVE seeing you.”
Chad winced. Yeah, he was sure of that!
“So what made you decide to finally wear a skirt today?” another woman asked. “You know, we’ve been making bets as to when you would do it?”
They were making bets on it? Crazier and crazier. “Uh… it’s complicated,” he replied, falling back on his same old answer.
“Everything to him is complicated lately,” Robin chimed in.
“Why?” several of the women asked.
“What’s so complicated?” one of the women asked him directly.
“It just is, that’s all!” Chad replied with a bit of anger. He wasn’t about to get into this any further.
“Well you don’t have to get so huffy about it,” the woman replied. “We’re all women here. We all have a lot of the same problems.”
“Well, I don’t!” Chad replied angrily.
“You don’t?” the woman asked. “You mean to tell me you don’t have to worry about getting your makeup on straight, or you don’t have to worry if your hair looks ok, or you don’t worry about your shoes hurting, or maybe a thousand other things? Don’t kid me, Honey.”
“Well… maybe,” Chad admitted.
“There, you see. You are one of us then. So spill girl, spill.”
But there was no way that Chad could tell them anything. He set his coffee on the table in front of him and stood up. “I can’t!” he said vehemently. He turned and forced his way between the women sitting around him.
“Let him go, girls” Robin said. “We’ll have him back again. I guarantee it!”
Chad turned and looked at her angrily then resumed making his way through the women and walked out.
“Bye bye, Sissy,” one of the women called behind him. “We’ll be here for you anytime!”
Chad stomped angrily back to his own cubicle, hating being exposed in the skirt he was wearing all the way. He literally couldn’t believe what they had just done to him. It was mean and cruel! Obviously Robin wasn’t the friend he thought she was. All the women were calling him Sissy now. Obviously Robin had told them. Things were definitely getting worse and worse!
He suddenly felt the need to pee and checked the dial on his watch to note the time. He sat in front of his computer to work, but work was impossible so he just stared at the screen while his mind raged.
“Hi Sissy.”
Chad turned around to see Robin standing in the entrance to his cubicle again. He angrily turned away from her, not wanting to talk or even look at her.
Robin walked in and leaned against his desk. “I hope you realize that what we just did was good for you.”
Chad turned to her aghast. “Good for me? You can’t be serious! That was the most cruel thing you could have ever done to me!” He turned away from her again.
“Cruel? Maybe. But it was good for you too. You not only need to get out more, but I hope you realize now that you have more friends out there than you realize. All you have to do is to talk to them and be their friend too.”
“Not likely!” he replied with his back still to her.
Robin sighed. “Like I said, whether you realize it or not. It was good for you and you’ve got friends there if you want them. I hope you’ll come back and join us again sometime.” She walked out then and left him.
Chad was still furious. Good for me? Ha! Friends? Ha! With friends like that, who needs enemies? The only thing they wanted to do was to humiliate me! Some friends!
A few minutes later, Chad’s mental ranting against Robin and her “friends” was interrupted by his realization that he needed to pee so badly. He was having trouble holding it back already. He was suddenly working too hard at it. Why bother? Why not just give in? It would feel so much better. The words self-respect, friends, and a life, ran through his head. He struggled against the need to pee, but he finally gave in and enjoyed wetting himself immensely. He checked his watch. Only eleven minutes. Not very good. Why was it suddenly so difficult to do? Why wasn’t it normal anymore? Next time though, he’d do better.

Friday, April 16, 2010

The Bet - Chapter 21 (Friday – week 3 Part 2 of 4)

The Bet
by Karen Singer

Chapter 21 (Friday – week 3 Part 2 of 4)

Mel tried hard to work with her clients, and mostly she did very well, but her mind was really on Chad. How was he doing today? What was he experiencing? What was going through his mind? Did he really like it – deep down underneath? She was betting that some part of him was. It was his fantasies after all.
Late in the morning, she went out to Andrea’s desk. “I’m going to be a little later than usual after lunch today,” she told her. “I’ve got a few things to do. But I’ll be back in plenty of time for my next appointment.”
“No problem,” Andrea replied as she looked carefully at Mel’s schedule for the day.
The door suddenly opened and they both watched as a delivery man came in with a fairly good sized box. Mel signed for it and they both watched till the delivery man left. There were no clients in the office. Mel picked the box up and started for her office, but she stopped and turned toward Andrea. “Want to see?”
“You don’t have to ask twice,” Andrea replied as she quickly got up from her desk.
Mel had no idea what was in the box, but she was betting it was another of the outfits she had ordered for Chad. She set it on her desk and attacked it with her scissors to open it. No mounds of ruffles escaped out of the box this time. Instead, she saw pale blue and white material wrapped up inside of plastic. She also saw a pair of socks, also wrapped in plastic, on top of everything. She pulled the socks out. They were fancy anklets trimmed with lots of pale blue lace. She giggled a bit and handed them to Andrea. Then she pulled out the main package. She was sure it was another dress, it was just wrapped up for shipping. But there was still another smaller box left in the main big box. She pulled out the smaller box and opened it. Inside was a pair of pale blue mary-jane shoes with tiny colorful flowers decorating the top. She couldn’t help but let out a giggle as she held them up for Andrea to see.
“How darling!” Andrea exclaimed as she started giggling too.
Mel handed the shoes to her while she attacked the plastic packaging around the dress. Finally she got it free and held it up. Free of the packaging, the skirt flared way out, supported underneath by a wealth of netting. While the dress didn’t have quite as many ruffles as the one that had arrived yesterday, it still had more than its fair share. The pale blue dress was heavily accented in white at the collar, the waist, the edges of the puffed sleeves and various places around the skirt. Without a doubt, it looked like a very sissyish little girl’s party dress.
“Oh, I love it!” Andrea screamed as she broke into complete laughter. I only wish I could see him in these things some time.
Mel was laughing too. “I’ll have to see what I can do about that sometime.”
“Promise?” Andrea asked, half kidding.
“Promise!” Mel replied, also kidding.

Robin stopped by Chad’s desk on her way to break. “Hi Chad,” she said as she walked into his cubicle. Chad turned around in his seat, but he didn’t say anything. At least he didn’t look as upset as he had been earlier. “I just wanted to see how you’re doing now, that’s all.” She was glad to see him actually smile – sheepishly, but still, he smiled.
“Better, I guess,” he replied. “Sorry I was so… off… earlier. It’s just that I was so worried about the way I’m dressed.”
“Why?” she asked. “You look great. Better than usual if you really want to know.”
“I do?”
He shook his head. “I don’t know why.”
“What do you mean?”
“Well, it’s just difficult… all this.”
“Look, Chad. Stand up so I can see you better.”
Chad hesitated for a moment, but what could it hurt to stand up? So he did as she asked.
Robin surveyed him carefully. “Yeah, you really do look a lot better. Especially with your hair fixed that way. In fact, I’ll bet there are times when nobody would even know you’re not a woman.”
“I don’t think I look that good,” he replied quickly.
“No. Well, not really. But I’m serious, at first glance, I don’t think anyone would know.”
He sat down again. Her assurance was comforting. “Thanks… I guess,” he added.
She smiled. “Want to go to break with me… seeing as how you’re completely dressed like the rest of us now?”
He looked up at her horrified. “No way! No thanks!”
She laughed. “Suit yourself,” she replied as she walked out.
Chad watched her go, then eventually turned back to his computer. But his project was no longer on his mind. He closed it and noticed the little icon he had put on his desktop for keeping track of the bet. He double-clicked on it and suddenly felt himself peeing as the spreadsheet opened. Peeing felt so good. So wonderfully good. He stared at the spreadsheet, only half seeing it. He was supposed to be keeping track of how long he could hold back. He had just peed without realizing he was going to do it. He hadn’t held back at all. Like he was truly incontinent. And he was loving every second of wetting himself.
Even though he was staring at the spreadsheet, he still wasn’t really seeing it. What he was seeing instead was what the spreadsheet represented – winning the bet. But did he really want to win the bet? He had just wet himself without knowing he was going to do it. He had completely forgotten to hold back. In fact, he realized that he hadn’t been holding back at all this morning, and he really didn’t want to. He thought again about his struggles to hold everything in yesterday, timing himself so carefully – for what? This felt normal, holding back didn’t – and it was difficult and somewhat painful. This was his dream – wetting himself with no control. Why did he really want to hold back at all? Why did he really want to win this bet?
The spreadsheet told him there were still forty-two days left. Was it worth all the trouble he had been going through to try to remain on track and win? He put down thirty eight minutes in the column next to the forty-two, his best time yesterday. It certainly didn’t seem like a very good number – not that he really cared today. Wetting himself with no control really did feel great. So why should he bother trying to win? It made no sense at all.
He closed the spreadsheet and glanced back out to the hallway. Nobody was there. No one had seen the spreadsheet. That was good. Not even Robin. Robin – his only friend. She was down with her other friends right now – probably laughing at him. But he had no other friends. Not anymore. Only her. And he figured that she was only his friend now because she had to work with him. And it felt bad. He felt ashamed at himself once again for what he was doing through this bet. He had lost the self-respect he used to have because of the things that Mel demanded that he do. Not only did nobody want to talk to him, but he was too ashamed of himself to talk to anyone else. Was this the fate he really wanted?
He quickly opened up his spreadsheet once again and started a new column. For the header he put “Reasons to Win The Bet!” The first item he listed was “self-respect.” Under that he added “friends.” And under that he wrote, “get a life,” because somehow, when this was all over with, he would get his life back again. He thought about those first three things on his list over and over again – self-respect, friends, get a life. He didn’t just want those things, he needed them. Finally, he started listing other things too, a pool table, a new computer, a washer and dryer, and lots of expensive furniture.
He finally closed the spreadsheet feeling once again in charge. Yeah, he loved wetting himself with no control, and maybe one day he’d do it again. But next time, he wouldn’t lose everything important in the process. Now he couldn’t wait to feel the tiny urge to pee again so he could start timing himself to see how long he could hold back!

Robin laughed along with all her friends. They all had been plying her with questions about Chad and the fact that he was wearing a skirt to work today.
“Oh God, I wish I had seen him this morning,” one of her friends lamented.
“Me too,” another one added.
“Well, I did see him,” still another one said. “And I’ve got to say, while I was surprised, I really thought he looked pretty good – from a distance mind you.”
Robin laughed again. “Yeah, he really doesn’t look all that bad – especially from a distance.”
“I just wish I had seen him,” one of the women repeated.
“Hey!” yet another one exclaimed. “I’ve got an idea!”

It was almost lunchtime by the time that Chad suddenly realized he had to pee. He had almost missed the faint signs. He quickly glanced at his watch to note the time, but a moment later, he felt himself peeing. He tried to hold back, but somehow, he couldn’t remember how. His brain was having trouble remembering where the connection was to those muscles again. He remembered having that same problem a few weeks ago when he had peed on the floor of his bathroom. He stood up and tried to figure out what was wrong. He didn’t really have any problem with it yesterday, it was just today. Ok, he was really enjoying wetting himself and that was great, but why couldn’t he remember how to contract those muscles? Did the fact that he had to wear a skirt to work today have any affect on him? He had overly worried about it all night. Could that have had anything to do with his problem? It didn’t seem likely, but he had no other explanation. He tried hard to figure out how to work those muscles, but he couldn’t seem to find them – still. Why not?
“Hi Chad,” Robin said as she walked past his cubicle on the way to lunch. “Going to the gym again?”
“Yeah,” he replied, still mystified by why he couldn’t find some of his muscles.
“Ok,” she replied. “Don’t forget to get me some brochures and prices.”
“Sure thing,” he replied as he pulled his purse out of his desk drawer, then turned his project off on his computer. As he walked through the hallways, he was still preoccupied with trying to figure out how to tighten his muscles. It was like they didn’t exist! It wasn’t till he was walking out the door that he noticed how many people were staring at him. Shit! He should have delayed a bit like he usually did till most of the people were gone. He hurried across the parking lot as fast as the heels on his feet would let him go – still trying to figure out how to tighten his muscles as he hurried.

Robin watched Chad carefully from her car as she waited for him. He was earlier than usual today. It was a good thing she had gotten a head start on him. She watched him pull out of his parking space, then she followed him. She knew exactly where he was going, so she allowed a few cars to get in-between. But it wasn’t very far to the gym. She saw Chad getting out of his car and reaching for his pink bag as she pulled into the parking lot.
Chad’s head was buried in his car as he reached for his bag so he didn’t see Robin till he was halfway to the door. He stopped, terrified that she was there. “What are you doing here?” he asked.
“I decided that it’s not right for you to get the information for me. I can get my questions answered much better if I do this myself.”
Her explanation sounded all too logical to him, but he still wasn’t exactly happy. “But I’ll be glad to get it all for you,” he argued.
“Why?” she replied. “I’m already here.” She linked her arm through his and practically dragged him toward the door.
He went with her, but not willingly. “Why this gym?” he asked.
“Oh Chad, what a question. It’s supposed to be a very good place and it’s right near work.”
He wasn’t really buying it though. “You just want to see who I’m meeting!”
She laughed a bit. “Well, that would be a bonus, I admit. But, I mean look at me! Since I had the baby I haven’t lost any weight at all.”
Chad wasn’t too sure about the last part. Robin had never seemed all that worried about her weight even before she had her baby. He was more certain that she just wanted to see who he was meeting. He stopped walking as they approached the door. Did he really want to do this? No, he didn’t. Things were embarrassing enough! “I can’t!” he replied as he turned around towards his car.
But Robin wasn’t about to let him get away that easily. He had been infuriatingly stubborn about things for the last few weeks. She was here now – with him and she wanted some answers. Even a few answers would help. She grabbed his arm before he could take another step. “Oh no you’re not! Don’t be silly. Now come on in with me while I see just how expensive this place is.
Chad was reluctant, but he let himself be dragged through the door that she opened for him.
“Sissy!” the receptionist squealed as she caught sight of him. “That’s a very pretty dress.”
“Sissy?” Robin asked in mock surprise as she turned her head towards him. She already knew about the name, but now she wanted him to tell her.
Chad looked at her and his mouth gaped open, but what could he say? How was he going to explain it? He turned his head back to the receptionist, she was just staring at him with an amused look on her face. He decided to ignore Robin. “Would you please find Cassie for me?”
The receptionist just folded her arms and stood there as if she was waiting for something. He realized that she wanted him to curtsey for her again, but there was no way he would ever do that with Robin there. “Please just get Cassie,” he repeated.
The receptionist didn’t look all that pleased. “I’ll be back to help you in a minute,” she said to Robin, then she left.
“Sissy?” Robin asked again.
He turned away from her, not wanting to say or admit anything.
But Robin stayed right behind him. “She called you Sissy. She didn’t say it as if she was calling you a sissy – which obviously you are. She said it like a name!” But he still wouldn’t face her. She saw him turn towards the door, as if he was going to run. She moved to stand between him and the door, blocking it, and also confronting his face.
“It’s complicated, damn it!” he exclaimed angrily.
“Why? What’s so damn complicated? Tell me!”
He turned away from her again. “No!”
He could be so infuriatingly stubborn. She was going to press him harder, but the receptionist was returning with another woman.
“Hi Sissy,” Cassie said as she got to the front. Her gaze though was on Robin. “Who’s your friend?”
Chad didn’t really want to introduce them. He didn’t want Robin there at all. But what was he going to do? Rather sullenly, he said, “Cassie, this is Robin. Robin, this is Cassie, one of the trainers here.”
“Glad to meet you Cassie,” Robin replied. “Are you any good at helping someone get rid of the extra pounds from having a baby?”
Cassie was clearly startled by Robin’s question. For a moment she had thought that maybe this Robin woman had come in for a different reason, seeing that she knew Sissy. She smiled broadly at Robin. “It’s one of my specialties. When did you have your baby?”
“Ten months ago. But I just never did anything to really get back into shape… not that I was in all that great shape to begin with – as you can probably see.”
Cassie smiled again. “Oh, you’re not bad at all.” She dropped her voice to almost a whisper. “You should see some of the women that come in here.”
Robin laughed along with Cassie, “Yeah, I can imagine. So what would you recommend?”
“Why don’t you let me give you the tour?”
Robin’s eyes opened wide with surprise. “That would be great!”
Chad suddenly found himself alone with the receptionist as he watched Robin following Cassie back through the gym. Maybe Robin really did want to join. But then again, maybe not! And now she knew that everyone here was calling him Sissy – his new name. Self-respect, friends, and a life!
“Your friend seems very nice,” the receptionist commented.
He shrugged. But the receptionist was right. “Yeah, she is,” he replied.
“I like what you’ve done with your hair today. It really looks very nice.”
Ugh! Small talk. Feminine small talk. “Thanks,” he replied. Why were Cassie and Robin taking so long? What could they be talking about? Not him, he hoped.
“Did you fix your hair yourself?” the receptionist asked.
He was forced to turn his attention back to her more fully. “Yeah,” he admitted. “It wasn’t all that easy.”
“Why not get it permmed then, like I do? Then it’s easy to take care of.”
Permmed? No, not if he could help it. “I don’t think I want to go that far with it,” he replied.
He finally spotted Cassie and Robin coming back together. They were talking animatedly together. He just hoped they weren’t talking about him.
“Thanks, Cassie,” Robin said as they got back to the front. “You’ve given me a lot to think about now. I’ll call you later.” She then turned her attention back towards Chad. Smiling, she said, “See you later – Sissy.” And she walked out the door.
Chad watched after her, totally aghast. He turned back to Cassie. “What did you tell her?”
Cassie was surprised. “Tell her? I told her all about the gym and what we can do for her here. She’s really interested and it would do her a lot of good.”
Chad still had a feeling that the two women had talked about more than just the gym. This time, he led the way to the back room himself.
Cassie watched him as he undressed. He didn’t seem all that happy. She was guessing the cause of his problem was the woman she had just met. She dug his bottle and the baby lotion out of his diaper bag and waited till he laid down on the floor, ready for her to begin. “You don’t seem very happy today,” she noted as she handed him his bottle.
“I’m not.”
“Because of your friend, Robin?”
He nodded instead of answering with the nipple in his mouth. Sucking on the nipple felt good, almost comforting.
Cassie removed his diapers and placed a fresh one under him. Then she squirted a large amount of baby lotion into her hands. “Ready?” she asked. Her only answer was him rolling his eyes. As usual, she began rubbing the baby lotion into him. She played with his chastity device just a bit to try to get a reaction out of him, but just like the past few days, she got nothing.
Chad felt her rubbing her magic hands over him. She really did have a wonderful touch. He wasn’t all that happy about when she started rocking his chastity device back and forth though, but fortunately, he never even started to get hard from it. But the moment her hands left his device, another sensation hit him, and unfortunately, it hit him quick.
“Oh no!” he shouted as he dropped the bottle in his hands and moved both of his hands to his groin. The feeling of having to pee came all too quickly and he still hadn’t been able to find those muscles to stop it. Before he knew it, it was all rushing out of him. He grabbed the chastity device and squeezed it hard to stop the peeing, but that did nothing at all. He rolled onto his side and got to his feet, still fighting to stop the peeing, but it was still coming out of him, and worse it was going everywhere because he wasn’t standing still.
“Stand still!” Cassie ordered as she quickly held a diaper over the chastity device.
Chad was breathing hard now, totally panicked once again while Cassie continued to hold the diaper to catch what little might still be coming out of him. He felt so frustrated. “Damn!” he cursed softly. He glanced around the small office. He had made a mess. Damn! “Sorry,” he exclaimed. “I couldn’t stop it.” Damn!
Cassie was somewhat annoyed since some of his pee had wound up on her, but mostly, she was surprised and fascinated. The guy really was losing control – totally! “It’s ok, baby,” she said as she cautiously removed the diaper to see if he had finished yet. He had. She looked around the room and grabbed another fresh diaper to wipe the mess up with. Fortunately, it all came up easily. Fortunately too, the cleaning lady washed all the floors in the gym every night. “See, no problem,” she finally said as she noticed that Chad was still on his feet and looking somewhat horrified. She supposed that she would look horrified too. “Come on, baby. Lay back down again and let’s just finish. Ok?”
Chad reluctantly laid back down again for her. He picked up his baby bottle and began sucking on it again. Why couldn’t he remember how to tighten those muscles? Did he have some kind of major accident that injured him in some way that he couldn’t remember? It made no sense.
Cassie didn’t play with his tiny asshole. Instead, she just put fresh baby lotion all over him and inserted another suppository. Then she diapered him. Through it all, he just drank his bottle and stared at the ceiling like he was very distracted. “Ok, all done,” she said, indicating that he could get dressed now. But it took him a moment to come back to reality. “Are you ok?” she asked.
“I don’t know,” he admitted. “I’m not having the best of days today.”
“Again?” she asked, referring to yesterday.
“Again,” he admitted.